Novel 2-phenyl-imidazoles and pharmaceutical compositions containing same

Abstract

The invention relates to novel 2-phenyl-imidazoles of the formula <IMAGE> (I) and the tautomers and acid addition salts thereof, particularly the pharmacologically acceptable acid addition salts, which exhibit valuable pharmacological properties, particularly an effect on the contractility of the heart muscle. The compounds of Formula I may be prepared by methods conventionally used for similar compounds.

We claim: 
     
       1. A compound of the formula ##STR15## wherein (a) A is nitrogen, B is hydroxymethine and D is methine; or (b) B is nitrogen, one of A and D is hydroxymethine and the other is methine;   R 1  is methylmercapto, methylsulfinyl, methylsulfonyl, aminosulfonyl, methylaminosulfonyl or dimethylaminosulfonyl;   R 2  is alkoxy of 1 to 3 carbon atoms; and   R 3  is hydrogen or methoxy; a pyridone tautomer thereof; or a non-toxic, pharmacologically acceptable acid addition salt thereof.     
     
     
       2. A compound of claim 1, which is of the formula ##STR16## wherein (a) A is nitrogen, B is hydroxymethine and D is methine; or (b) B is nitrogen, one of A and D is hydroxymethine and the other is methine;   R 1  is methylmercapto, methylsulfinyl, methylsulfonyl, aminosulfonyl, methylaminosulfonyl or dimethylaminosulfonyl; and   R 2  is alkoxy of 1 to 3 carbon atoms; a pyridone tautomer thereof; or a non-toxic, pharmacologically acceptable acid addition salt thereof.     
     
     
       3. A compound of claim 1, which is of the formula ##STR17## wherein R 1  is methylmercapto, methylsulfinyl, methylsulfonyl, aminosulfonyl, methylaminosulfonyl or dimethylaminosulfonyl; R 2  is alkoxy of 1 to 3 carbon atoms; and   R 3  is hydrogen or methoxy; a pyridone tautomer thereof; or a non-toxic, pharmacologically acceptable acid addition salt thereof.     
     
     
       4. A compound of claim 3, which is of the formula ##STR18## wherein R 1  is methylmercapto, methylsulfinyl, methylsulfonyl, aminosulfonyl, methylaminosulfonyl or dimethylaminosulfonyl; and R 2  is alkoxy of 1 to 3 carbon atoms; a pyridone tautomer thereof; or a non-toxic, pharmacologically acceptable acid addition salt thereof.     
     
     
       5. A compound of claim 4, where R 1  is aminosulfonyl, methylaminosulfonyl or dimethylaminosulfonyl; and   R 2  is methoxy; a pyridone tautomer thereof; or a non-toxic, pharmacologically acceptable acid addition salt thereof.     
     
     
       6. A non-toxic, pharmacologically acceptable acid addition salt of a compound of claim 1 formed with an inorganic or organic acid. 
     
     
       7. A compound of claim 1, which is 2-(2-methoxy-4-methylsulfonyl-phenyl)-4H-imidazo[4,5-b]pyridine-5-one, a tautomer thereof or a non-toxic, pharmacologically acceptable acid addition salt thereof. 
     
     
       8. A compound of claim 1, which is 2-(2-methoxy-4-methylmercapto-phenyl)-4H-imidazo[4,5-b]pyridine-5-one, a tautomer thereof or a non-toxic, pharmacologically acceptable acid addition salt thereof. 
     
     
       9. A compound of claim 1, which is 2-(2-methoxy-4-dimethylaminosulfonyl-phenyl)-4H-imidazo[4,5-b]pyridine-5-one, a tautomer thereof or a non-toxic, pharmacologically acceptable acid addition salt thereof. 
     
     
       10. A cardiotonic pharmaceutical composition consisting essentially of an inert pharmaceutical carrier and an effective cardiotonic amount of a compound of claim 1. 
     
     
       11. The method of treating cardiac insufficiency in a warm-blooded animal in need of such treatment, which comprises perorally, parenterally or rectally administering to said animal an effective cardiotonic amount of a compound of claim 1.